DE602004007672T2 - Zur behandlung von zns-erkrankungen geeignete piperazinylchinolinderivate - Google Patents

Zur behandlung von zns-erkrankungen geeignete piperazinylchinolinderivate Download PDF

Info

Publication number: DE602004007672T2
Authority: DE; Germany
Prior art keywords: alkyl; compound; formula; heteroaryl; hydrogen
Prior art date: 2003-09-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

DE602004007672T

Other languages

German (de)

English (en)

Other versions

DE602004007672D1 (de

Inventor

Christopher Norbert GlaxoSmithKl JOHNSON

Stephen Frederick GlaxoSmithKl MOSS

David R GlaxoSmithKl WITTY

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Glaxo Group Ltd

Original Assignee

Glaxo Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-09-25

Filing date

2004-09-23

Publication date

2008-04-10

2004-09-23 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2007-08-30 Publication of DE602004007672D1 publication Critical patent/DE602004007672D1/de

2008-04-10 Application granted granted Critical

2008-04-10 Publication of DE602004007672T2 publication Critical patent/DE602004007672T2/de

2024-09-24 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000011282 treatment Methods 0.000 title claims abstract description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 9
201000010099 disease Diseases 0.000 title 1
XRXDAJYKGWNHTQ-UHFFFAOYSA-N quipazine Chemical class C1CNCCN1C1=CC=C(C=CC=C2)C2=N1 XRXDAJYKGWNHTQ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 82
239000001257 hydrogen Substances 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 29
-1 cyano radicals Chemical class 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
125000001072 heteroaryl group Chemical group 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
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208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
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125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 2
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125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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ZQYIVVZJNWCUSE-UHFFFAOYSA-N 3-[(3-chlorophenyl)methyl]-8-piperazin-1-ylquinoline Chemical compound ClC1=CC=CC(CC=2C=C3C=CC=C(C3=NC=2)N2CCNCC2)=C1 ZQYIVVZJNWCUSE-UHFFFAOYSA-N 0.000 claims 1
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125000005422 alkyl sulfonamido group Chemical group 0.000 claims 1
238000000034 method Methods 0.000 abstract description 18
239000000203 mixture Substances 0.000 abstract description 15
238000002360 preparation method Methods 0.000 abstract description 7
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230000000144 pharmacologic effect Effects 0.000 abstract description 3
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238000006243 chemical reaction Methods 0.000 description 12
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238000001819 mass spectrum Methods 0.000 description 11
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229910052786 argon Inorganic materials 0.000 description 9
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208000035475 disorder Diseases 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
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MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
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239000002253 acid Substances 0.000 description 6
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238000007792 addition Methods 0.000 description 5
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239000011630 iodine Substances 0.000 description 5
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HJKYXKSLRZKNSI-UHFFFAOYSA-I pentapotassium;hydrogen sulfate;oxido sulfate;sulfuric acid Chemical compound [K+].[K+].[K+].[K+].[K+].OS([O-])(=O)=O.[O-]S([O-])(=O)=O.OS(=O)(=O)O[O-].OS(=O)(=O)O[O-] HJKYXKSLRZKNSI-UHFFFAOYSA-I 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Addiction (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Psychology (AREA)
Obesity (AREA)
Vascular Medicine (AREA)
Child & Adolescent Psychology (AREA)
Diabetes (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Anesthesiology (AREA)
Nutrition Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)

DE602004007672T 2003-09-25 2004-09-23 Zur behandlung von zns-erkrankungen geeignete piperazinylchinolinderivate Expired - Fee Related DE602004007672T2 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB0322510		2003-09-25
GBGB0322510.9A GB0322510D0 (en)	2003-09-25	2003-09-25	Novel compounds
PCT/EP2004/010845 WO2005030724A1 (fr)	2003-09-25	2004-09-23	Derives de piperazinyl-quinoline utilises pour le traitement des troubles du systeme nerveux central

Publications (2)

Publication Number	Publication Date
DE602004007672D1 DE602004007672D1 (de)	2007-08-30
DE602004007672T2 true DE602004007672T2 (de)	2008-04-10

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DE602004007672T Expired - Fee Related DE602004007672T2 (de)	2003-09-25	2004-09-23	Zur behandlung von zns-erkrankungen geeignete piperazinylchinolinderivate

Country Status (8)

Country	Link
US (1)	US7439243B2 (fr)
EP (1)	EP1663981B1 (fr)
JP (1)	JP2007506704A (fr)
AT (1)	ATE367380T1 (fr)
DE (1)	DE602004007672T2 (fr)
ES (1)	ES2289563T3 (fr)
GB (1)	GB0322510D0 (fr)
WO (1)	WO2005030724A1 (fr)

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PT1956004E (pt)	2002-03-27	2012-08-31	Glaxo Group Ltd	Derivados de quinolina e sua utilização como ligandos 5-ht6
PL1558582T3 (pl)	2003-07-22	2006-05-31	Arena Pharm Inc	Diarylowe i aryloheteroarylowe pochodne mocznika jako modulatory receptora serotoninowego 5-HT2A użyteczne w profilaktyce i w leczeniu zaburzeń związanych z tym receptorem
GB0425548D0 (en) *	2004-11-19	2004-12-22	Glaxo Group Ltd	Radiolabelled ligands
ATE465151T1 (de) *	2005-07-27	2010-05-15	Hoffmann La Roche	4-aryloxy-chinolin-derivate als 5-ht6-modulatoren
US8927546B2 (en)	2006-02-28	2015-01-06	Dart Neuroscience (Cayman) Ltd.	Therapeutic piperazines
AU2007221021B2 (en) *	2006-02-28	2013-01-17	Dart Neuroscience (Cayman) Ltd	Therapeutic piperazines as PDE4 inhibitors
US20100041672A1 (en) *	2007-03-21	2010-02-18	Glaxo Group Limited	Use of quinoline derivatives in the treatment of pain and irritable bowel syndrome
WO2009019286A1 (fr) *	2007-08-07	2009-02-12	Abbott Gmbh & Co. Kg	Composés de quinoléine appropriés pour traiter les affections sensibles à la modulation des récepteurs sérotoninergiques 5-ht6
US9084742B2 (en)	2007-12-12	2015-07-21	Axovant Sciences Ltd.	Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-Quinoline
WO2009123714A2 (fr)	2008-04-02	2009-10-08	Arena Pharmaceuticals, Inc.	Procédés de préparation de dérivés de pyrazole utiles comme modulateurs du récepteur de la sérotonine 5-ht<sb>2a</sb>
WO2010062321A1 (fr)	2008-10-28	2010-06-03	Arena Pharmaceuticals, Inc.	Procédés utiles pour la préparation de 1-[3-(4-bromo-2-méthyl-2h-pyrazol-3-yl)-4-méthoxy-phényl]-3-(2,4-difluoro‑phényl)-urée, et formes cristallines associées
AU2013385618B2 (en)	2013-04-02	2017-01-05	Annji Pharmaceutical Co., Ltd.	Multifunctional quinoline derivatives as anti-neurodegenerative agents
US9302992B2 (en)	2013-04-02	2016-04-05	Annji Pharmaceutical Co., Ltd.	Multifunctional quinoline derivatives as anti-neurodegenerative agents
EP3027613B1 (fr)	2013-07-25	2018-03-28	Uniwersytet Jagiellonski	Dérivés de pyrroloquinoline comme antagonistes de 5-ht6, son procédé de préparation et son utilisation
MX388281B (es)	2015-06-12	2025-03-11	Axovant Sciences Gmbh	Derivados de diaril y arilheteroaril urea como moduladores del receptor 5ht2a de serotonina útiles para la profilaxis y el tratamiento de un trastorno conductual del sueño rem.
CA2992518A1 (fr)	2015-07-15	2017-01-19	Axovant Sciences Gmbh	Derives d'arylheretoaryl uree en tant que modulateurs du recepteur serotoninergique 5-ht2a utiles pour la prophylaxie et le traitement d'hallucinations associees a une maladie neurodegenerative
WO2019180176A1 (fr)	2018-03-21	2019-09-26	Spherium Biomed, S.L.	Composition pour le traitement de la schizophrénie et/ou de la psychose

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US6313126B1 (en) *	1999-01-07	2001-11-06	American Home Products Corp	Arylpiperazinyl-cyclohexyl indole derivatives for the treatment of depression
MXPA03006250A (es)	2001-01-16	2003-09-22	Astrazeneca Ab	Compuestos heterociclicos terapeuticos.
JP2005506368A (ja)	2001-10-23	2005-03-03	ビオヴィトルム・アクチボラゲット	肥満の処置におけるまたは食物摂取の減少のためのインドールおよびインドリン誘導体の使用
PT1956004E (pt)	2002-03-27	2012-08-31	Glaxo Group Ltd	Derivados de quinolina e sua utilização como ligandos 5-ht6
US7943639B2 (en) *	2002-06-20	2011-05-17	Proximagen Limited	Compounds

2003
- 2003-09-25 GB GBGB0322510.9A patent/GB0322510D0/en not_active Ceased
2004
- 2004-09-23 DE DE602004007672T patent/DE602004007672T2/de not_active Expired - Fee Related
- 2004-09-23 EP EP04787037A patent/EP1663981B1/fr not_active Expired - Lifetime
- 2004-09-23 WO PCT/EP2004/010845 patent/WO2005030724A1/fr not_active Ceased
- 2004-09-23 US US10/572,671 patent/US7439243B2/en not_active Expired - Fee Related
- 2004-09-23 ES ES04787037T patent/ES2289563T3/es not_active Expired - Lifetime
- 2004-09-23 JP JP2006527375A patent/JP2007506704A/ja not_active Withdrawn
- 2004-09-23 AT AT04787037T patent/ATE367380T1/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
US7439243B2 (en)	2008-10-21
JP2007506704A (ja)	2007-03-22
WO2005030724A1 (fr)	2005-04-07
ATE367380T1 (de)	2007-08-15
EP1663981A1 (fr)	2006-06-07
GB0322510D0 (en)	2003-10-29
DE602004007672D1 (de)	2007-08-30
US20070027139A1 (en)	2007-02-01
ES2289563T3 (es)	2008-02-01
EP1663981B1 (fr)	2007-07-18

Publication	Publication Date	Title
DE602004007672T2 (de)	2008-04-10	Zur behandlung von zns-erkrankungen geeignete piperazinylchinolinderivate
DE60014083T2 (de)	2006-03-02	Substituierte heterocyclylkondensierte gamma carboline
JP4455064B2 (ja)	2010-04-21	キノリン誘導体および５−ｈｔ６リガンドとしてのその使用
DE69513219T2 (de)	2000-03-23	Kondensierte heterocyclische Verbindungen, ihre Herstellung und Anwendung
EP0546388B1 (fr)	1996-03-27	Azahétérocyclylméthyl-chromanes comme agents pour le traitement de maladies du système nerveux central
DE60212841T2 (de)	2007-06-21	4 piperazinylindolderivate mit affinität zum 5-ht6-rezeptor
DE69830405T2 (de)	2006-01-26	Sulfonamid-derivate als 5-ht6 receptor antagonisten und verfahren zu ihrer herstellung
DE60309852T2 (de)	2007-06-06	Chinolin- und aza-indolderivate und deren verwendung als 5-ht6 liganden
DE60208221T2 (de)	2006-08-03	Heterozyklische verbindungen zur behandlung von harnwegserkrankungen
DE602004003927T2 (de)	2007-06-28	Verbindungen mit aktivität am 5ht2c-rezeptor und anwendungen davon
EP0013894B1 (fr)	1982-02-03	Aryléthers, procédé pour leur préparation et médicaments les contenant
DE69820102T2 (de)	2004-07-15	Substituierte chromanderivate
DE60304695T2 (de)	2006-09-21	7-arylsulfonamido-2,3,4,5-tetrahydro-1h-benzo[d]azepin-derivate mit 5-hat-6-rezeptor affinität zur behandlung von erkrankungen des zentralnervensystems
DE69820103T2 (de)	2004-09-02	Substituierte chromanderivate
DE60316180T2 (de)	2008-05-29	Aminoalkoxyindol-derivate als 5-ht6-rezeptorliganden zur bekämpfung von zns-krankheiten
EP1660483B1 (fr)	2008-12-24	Derives de 8- (1-piperazinyl)- quinoleine et leur utilisation pour le traitement de troubles du systeme nerveux central
EP1140898A1 (fr)	2001-10-10	Derives d'amide et d'uree s'utilisant comme inhibiteurs de reabsorption de 5-ht et comme ligands de 5-ht1b/1d
DE602004004378T2 (de)	2007-05-31	Verbindungen mit einer 5-ht2c rezeptor-wirkung und ihre verwendung
DE69029954T2 (de)	1997-05-28	Pyridinderivate
DE69411589T2 (de)	1999-01-07	Indol, indolin und chinolin derivate mit einer 5ht1d antagonistischen wirkung
EP0546389B1 (fr)	1996-04-17	Dérivés de chromane pipéridylméthyl substitués comme agents pour le traitement de maladies du système nerveux central
DD149069A5 (de)	1981-06-24	Verfahren zur herstellung neuer piperidinopropylerivate
IE922090A1 (en)	1992-12-30	2-(1-piperidyl)ethanol derivatives, their preparation and¹their therapeutic application
DE9101348U1 (de)	1991-06-06	Trizyklisch-zyklische Amine als neue Cholinesterease-Inhibitoren
DD271517A5 (de)	1989-09-06	Verfahren zur herstellung von neuen naphthylderivaten

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2008-08-07	8364	No opposition during term of opposition
2010-07-22	8339	Ceased/non-payment of the annual fee